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Synthesis 2006(8): 1221-1245  
DOI: 10.1055/s-2006-926404
REVIEW
© Georg Thieme Verlag Stuttgart · New York

Recent Advances in Cyclopropene Chemistry

Michael Rubina, Marina Rubinaa, Vladimir Gevorgyan*b
a University of Kansas, Department of Chemistry, 1251 Wescoe Hall Drive, Lawrence, KS 66045, USA
Fax: +1(785)8645396; e-Mail: mrubin@ku.edu;
b University of Illinois at Chicago, Department of Chemistry, 845 West Taylor Street, Chicago, IL 60607, USA
Fax: +1(312)3550836; e-Mail: vlad@uic.edu;
Further Information

Publication History

Received 26 September 2005
Publication Date:
27 March 2006 (online)

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Abstract

In this review, a brief outline of synthetic methods toward cyclopropenes is provided. Main emphasis is placed on transformations of cyclopropenes proceeding with preservation of the ring, with a spotlight on recent developments in this area.

1 Introduction

2 Synthesis of Cyclopropenes: An Overview

3. Chemistry of Cyclopropenes

3.1 Formal Substitution Reactions

3.1.1 Cyclopropenes as Nucleophilic Species

3.1.2 Cyclopropenes as Electrophilic Species

3.1.3 Substitution via Cyclopropenylium Species

3.2 Additions across the Double Bond of Cyclopropene

3.2.1 Additions of H-H Moiety

3.2.2 Additions of H-C Moieties

3.2.3 Additions of H-M Moieties

3.2.4 Additions of C-M Moieties

3.2.5 Additions of M-M Moieties

3.3 Cycloadditions

3.3.1 [2+1] Cycloadditions

3.3.2 [3+2] Cycloadditions

3.3.3 [2+2+1] Cycloadditions

3.3.4 [4+2] Cycloadditions

4. Conclusions

Key words

cyclopropenes - hydrometalation - carbometalation - cycloaddition­

87

Rubina, M.; Rubin, M.; Gevorgyan, V. unpublished results.

101

For computations of MO in 3-vinylcyclopropenes, see ref. 48.